Holiday (1930)

Stars: Ann Harding, Mary Astor, Edward Everett Horton
Director: Edward H. Griffith

Remade in 1938 by George Cukor with Katharine Hepburn, Cary Grant, and (again) Edward Everett Horton.

A young man falls in love with a girl from a rich family. His unorthodox plan to go on holiday for the early years of his life is met with skepticism by everyone except for his fiancée's eccentric sister and long suffering brother.